OXALIC ACID DERIVATIVES, THEIR PREPARATION AND PLANT GROWTH REGULATORS CONTAINING THEM

DERIVES DE L'ACIDE OXALIQUE, LEUR PREPARATION ET REGULATEURS DE LA CROISSANCE DES PLANTES LES RENFERMANT

English Abstract

O.Z. 0050/41753
ABSTRACT OF THE DISCLOSURE: Oxalylhydroxamic acid derivatives of the
formula I
R1-ON(R2)-Co-Co-X-R3 I,
where the substituents have the following meanings:
X is oxygen or sulfur;
R1 is substituted or unsubstituted alkyl, alkenyl or alkynyl;
substituted or unsubstituted monocyclic or polycyclic cycloalkyl or
cycloalkylmethyl;
substituted or unsubstituted phenyl or phenyl-C1-C4-alkyl;
R2 is hydrogen or alkyl;
R3 is substituted or unsubstituted alkyl, alkenyl or alkynyl;
substituted or unsubstituted monocyclic or polycyclic cycloalkyl;
substituted or unsubstituted phenyl-C1-C4-alkyl or phenoxy-C1-C4-
alkyl;
and their agriculturally useful salts; their manufacture; growth-regulat-
ing agents containing them; and methods of regulating plant growth.

Claims

42 O.Z. 0050/41753
What we claim is:
1. Oxalylhydroxamic acid derivatives of the formula
R1-ON(R2)-CO-CO-X-R3 I,
where the substituents have the following meanings:
X is oxygen or sulfur;
R1 is C3-C18-alkenyl or C3-C8-alkynyl, where these groups may carry
from one to five halogen atoms;
monocyclic or polycyclic C3-C10-cycloalkyl or C3-C10-cycloalkyl-
methyl, where these rings may carry from one to three C1-C4-alkyl
groups and/or one phenyl ring; or
phenyl, where the aromatic radical may carry from one to five
halogen atoms and/or from one to three of the following groups:
nitro, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-halo-
alkoxy, C1-C4-alkylthio and C1-C4-haloalkylthio;
R2 is hydrogen, C1-C4-alkyl, C3-C4-alkenyl or benzyl, where the
aromatic radical may carry from one to five halogen atoms and/or
from one to three of the following groups: C1-C4-alkyl, C1-C4-
haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio and
C1-C4-haloalkylthio;
R3 is C1-C20-alkyl which may carry from one to five halogen atoms
and/or from one to three of the following groups: cyano, C1-C10-
alkoxy, C1-C4-haloalkoxy, C1-C4-alkytthio, C1-C4-haloalkylthio,
C3-C10-cycloalkyl, C3-C10-cycloalkoxy, C3-C10-cycloalkylthio and
C3-C12-alkenyloxy;
C3-C18-alkenyl or C3-C8-alkynyl, where these groups may carry
from one to five halogen atoms;
monocyclic or polycyclic C3-C10-cycloalkyl which may carry from
one to three C1-C4-alkyl groups;
phenyl-C1-C4-alkyl or phenoxy-C1-C4-alkyl, where the aromatic
radicals may carry from one to five halogen atoms and/or from one
to three of the following groups: nitro, C1-C4-alkyl, C1-C4-
haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio and
C1-C4-haloalkylthio;
and agriculturally useful salts thereof.

43 O.Z. 0050/41753
2. Compounds of the formula I as set forth in claim 1, where R1 is
C3-C18-alkenyl or C3-C8-alkynyl, each of which may carry from one to
five halogen atoms.
Compounds of the formula I as set forth in claim 1, where R3 is one of
the following radicals:
C1-C20-alkyl, C3-C18-alkenyl or C3-C8-alkynyl, where these groups may
carry from one to five halogen atoms, or
monocyclic or polycyclic C3-C10-cycloalkyl or C3-C10-cycloalkylmethyl
which may carry from one to three C1-C4-alkyl groups.
A process for the manufacture of compounds of the formula I as set
forth in claim 1, where an oxalyl ester halide of the formula II
Hal-CO-CO-X-R3 II
where Hal is a halogen atom, is reacted in conventional manner in an
inert organic solvent in the presence of a base with a hydroxylamine
of the formula III
R1-ON(R2)-H III.
A process for the manufacture of compounds of the formula I as set
forth in claim 1, wherein an oxalylhydroxylamine of the formula IV
HON(H)-CO-CO-X-R3 IV
is reacted in conventional manner in an inert organic solvent initial-
ly with an alkylating agent of the formula V,
R1-Y V,
where Y is a nucleophilically displaceable leaving group, and, where
R2 is not hydrogen, the oxalylhydroxamic acid derivative Ia thus
obtained
R1-ON(H)-CO-CO-X-R3 Ia
is reacted in conventional manner in an inert organic solvent with an
alkylating agent of the formula VI,
R2-Y VI,
where Y is a nucleophilically displaceable leaving group.

44 O.Z. 0050/41753
An agent for regulating the growth of plants and which contains an
oxalylhydroxamic acid derivative of the formula I as set forth in
claim 1, and inert additives.
A method of regulating the growth of plants, wherein the plants, their
habitat and/or their seed are treated with a regulatorily active
amount of an oxalylhydroxamic acid derivative of the formula IA
R1-ON(R2)-Co-co-x-R3 IA,
where the substituents have the following meanings:
X is oxygen or sulfur;
R1 is C1-C20 alkyl, C3-C18-alkenyl or C3-C8-alkynyl, where these
groups may carry from one to five halogen atoms;
C2-C8-alkyl carrying a C1-C12-alkoxy group;
monocyclic or polycyclic C3-C10-cycloalkyl or C3-C10-cycloalkyl-
methyl, where these rings may carry from one to three C1-C4-alkyl
groups and/or one phenyl ring;
phenyl or phenyl-C1-C4-alkyl, where the aromatic radicals may
carry from one to five halogen atoms and/or from one to three of
the following groups: nitro, C1-C4-alkyl, C1-C4-haloalkyl,
C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio and C1-C4-halo-
alkylthio;
R2 is hydrogen, C1-C4-alkyl, C3-C4-alkenyl or benzyl, where the
aromatic radical may carry from one to five halogen atoms and
from one to three of the following groups: C1-C4-alkyl, C1-C4-
haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio and
C1-C4-haloalkylthio;
R3 is C1-C20-alkyl which may carry from one to five halogen atoms
and/or from one to three of the following groups: cyano, C1-C10-
alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio,
C3-C10-cycloalkyl, C3-C10-cycloalkoxy, C3-C10-cycloalkylthio and
C3-C12-alkenyloxy;
C3-C18-alkenyl or C3-C8-alkynyl, where these groups may carry
from one to five halogen atoms;

O.Z. 0050/41753
monocyclic or polycyclic C3-C10-cycloalkyl which may carry from
one to three C1-C4-alkyl groups;
phenyl-C1-C4-alkyl or phenoxy-C1-C4-alkyl. where the aromatic
radicals may carry from one to five halogen atoms and/or from one
to three of the following groups: nitro, C1-C4-alkyl, C1-C4-
haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio and
C1-C4-haloalkylthio.

Description

2Q~759
O.Z. 0050/41753
Oxalic acid derivatives, their Preparation and Plant
rowth requlators containinq them
The present invention relates to oxalylhydroxamic
acid derivatives of the general formula I
S R1~oN(R2)-co-co-x-R3
where
X is oxygen or sulfur;
R1 is C3-Clg-alkenyl or C3-Cg-alkynyl, where these groups
may carry from one to five halogen atoms,
monocyclic or polycyclic C3-C10-cycloalkyl or C3-Clo-cyclo-
alkylmethyl, where these rings may carry from one to
three Cl-C4-alkyl groups and/or one phenyl ring,
or phenyl, where the aromatic radical may carry from one
to five halogen atoms and/or from one to three of the
following groups: nitro, C1-C4-alkyl, C1-C4-haloalkyl,
Cl-C4-alkoxy,
C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio;
R2 is hydrogen, Cl-C4-alkyl, C3- or C4-alkenyl or benzyl,
where the aromatic radical may carry from one to five
halogen atoms and/or from one to three of the following
groups: Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy,
C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio;
R3 is Cl-C2D-alkyl which may carry from one to five halogen
atoms and~or from one to three of the following groups:
cyano, Cl-C1O-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio,
Cl-C4-haloal]cylthio, C3-C10-cycloalkyl, C3-C10-cycloalkoxy,
C3-C1O-cycloalkylthio or C3-Cl2-alkenyloxy,
C3-Cla-alkenyl or C3-Cl3-alkynyl, where these groups may
carry from one to five halogen atoms,
monocyclic or polycyclic C3-Cl3-cycloalkyl which may car~y
from one to three C1-C4-alkyl groups, or
phenyl-Cl-C4-alkyl or phenoxy-Cl-C4-alkyl, where the
aromatic radicals may carry from one to five halogen
atom~ and/or from one to three of the following groups:
nitro, Cl-C4-alkyl, Cl-C~-haloalkyl, Cl-C4-alkoxy,
Cl-C4-haloalkoxy, Cl-C4-alkylthio or Cl-C~-haloalkylthio,

2~759
- 2 - O.Z. 0050/41753
and their agriculturally useful salts.
The present invention furthermore relates to
processes for the preparation of these compounds, agents
containing them and methods for using oxalylhydroxamic
acid derivatives of the general formula IA
Rl-oN(R2)-co-co-x-R3 IA
where
X i~ oxygen or sulfur;
Rl is Cl-C20-alkyl, C3-C18-alkenyl or C3-C~-alkynyl, where
these groups may carry from one to five halogen atoms,
C2-C8-alkyl which carries a Cl-Cl2-alkoxy group,
monocyclic or polycyclic C3-C10-cycloalkyl or C3-C1o-cyclo-
alkylmethyl, where these ring may carry from one to
three Cl-C~ alkyl groups and/or one phenyl ring,
or phenyl or phenyl-Cl-C4 alkyl, where the aromatic
radical~ may carry from one to five halogen atom~ and/or
from one to three of the following groups: nitro,
Cl-C4-alk~rl, Cl-C4-haloalkyl, Cl C4-alkoxy,
Cl-C4-haloalkoxy, Cl-C4-alkylthio or Cl-C4-haloalkylthio;
R2 is hydrogen, Ci-C4-al~yl, C3- or C4-alkenyl or benzyl,
where the aromatic radical may carry from one to five
halogen atom~ and/or from one to three of the following
groups: Cl-C~-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy,
C1-C4-haloalkoxy, Cl-C4-alkylthio or Cl-C4-haloalkylthio;
R3 ig Cl-C20-alkyl which may carry from one to five halogen
atom~ and~or from one to three of the following groups:
cyano, Cl-C1O-alkoxy, Cl-C4-haloalkoxy, Cl-C4-alkylthio,
'Cl-C4-haloalkylthio, C3-C10-cycloalkyl, C3-Cl~,-cycloalkoxy,
C3-C10-cycloalkylthio or C3-C12-alkenyloxy,
C3-Cl8-alkenyl or C3-C~-alkynyl, where the~e groups may
carry from one to five halogen atoms,
monocyclic or polycyclic C3-C10-cy~loalkyl which may carry
from one to three Cl-C4-alkyl groups, or
phenyl-Cl-C4-alkyl or phenoxy-Cl-C4-alkyl, where the
aromatic radicals may carry rom one to five halogen
atoms and/or from one to three of the following groups:
nitro, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy,

2 ~ 9
- 3 - 0.Z. 0050/41753
Cl-C4-haloalkoxy, Cl-C4-alkylthio or Cl-C4-haloalkylthio,
as plant growth regulato~s.
Oxalylhydroxamic acid derivatives are disclosed
in the literature as intermediates for syntheses. For
example, ethyl (methoxyamino)-o~oacetate, ethyl (ethoxy-
amino)-oxoacetate, ethyl (isopropoxyamino)-oxoacetate and
ethyl (benzyloxyamino)-oxoacetate are disclosed in the
technical literature (cf. for example M. Takebayashi et
al., Bull. Chem. Soc. Japan 45 (1972), 3567, and D.
Geffken et al., Chemiker Zeitg. lû9 (1985), 190).
CA-A 2,002,021 also describes the microbicidal
and herbicidal action of oxalylhydroxamic acid derivati-
ves whose general formula encompasses compounds I defined
above. However, a growth-regulating action of such com-
pounds has hitherto not been disclosed.
It is an ob~ect of the present invention to
provide novel active herbicide and plant growth
regulators.
Wa have found that thi~ ob~ect is achieved by the
oxalylhydroxamic acid derivatives I defined at the
outset.
We have also found proces~e~ for the preparation
of these oxalylhydroxamic derivativeY, agent containing
them and methods for using the oxalylhydroxamic deriva-
tives IA, which are likewise defined at the outset.
Th~ oxalylhydrox~mic ~cid derivatives I areobtainable by variou~ method~. They are particularly
advantageouYly obtained by one of the processes A or B
described below.
Process A.
The oxalylhydroxamic acid derivatives of the
formula I are obtained, for example, by reacting an
oxalyl ester halide of the general formula II with a
hydroxylamine of the general for~ula III in a convention-
al manner in an 'iner~ organic solvent in the preYence ofa base~
Hal-CO-CO-X-R3 + R1-oH(R2)-H Rl-ON(R2)-CO-CO-X-R3
II III I

2~67J9
- 4 - O.Z. 0050/41753
In the formula II, Hal is halogen, such as fluorine,
chlorine, bromine or iodine, preferably chlorine or
bromine.
The reaction is carried out in general at from
-20 to 120C, preferably from 0 to 80C.
Examples of suitable solvents are halohydro-
carbons, in particular chlorohydrocarbons, eg. 1,1,2,2-
tetrachloroethylene or l,1,2,2-tetrachloroethane,
dichloropropane, methylene chloride, dichlorobutane,
chloroform, chloronaphthalene, dichloronaphthalene,
carbon tetrachloride, 1,1,1- or 1,1,2-trichloroethane,
trichloroethylene, pentachloroethane, o-, m- or p-
difluorobenzene, 1,2-dichloroethane, l,l-dichloroethane,
1,2-cis-dichloroethylene, chlorobenzene, fluorobenzene,
bromobenzene, iodobenzene, o-, m- or p-dichloro~enzene,
o-, p- or m-dibromobenzene, o-, m- or p-chlorotoluene, or-
1,2,4-trichlorobenzene; ethers, eg. ethyl propyl ether,
methyl tert-butyl ether, n-butyl ethyl ether, di-n-butyl
ether, diisobutyl ether, diisoamyl ether, diisopropyl
ether, anisole, phenetole, cyclohexyl methyl ether,
diethyl ether, ethylene glycol dimethyl ether, tetra-
hydrofuran, dioxane or thioanisole; nitrohydrocarbons,
such as nitromethane, nitroethane, nitrobenzene, o-, m-
or p-cnloronitrobenzene or o-nitrotoluene; nitriles, such
as acetonitrile, butyronitrile, isobutyronitrile, benzo-
nitrile, m-chlorobenzonitrile; aliphatic or
cycloaliphatic hydrocarbons, eg. heptane, pinane, nonane,
o-, m- or p-cymene, gasoline fractions boiling within a
range from 70 to 190C, cyclohexane, methylcyclohexane,
decalin, petroleum ether, hexane, naphtha, 2,2,4-
trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-
trimethylpentane or octane; esters, such as e.g. ethyl
acetate, ethyl ace~oacetate or isobutyl acetate, amides,
eg. formamide, methylformamide or dimethylformamide;
ketones, eg. acetone ox methyl ethyl ketone, and, if
necessary also water and corresponding mixtures. It is
also possible to use the compound of the formula III in

7 .5 9
- 5 - o. Z . 0050/41753
excess as the solvent.
The solvent is advantageously used in an amount
of from 100 to 2,000, preferably from 200 to 700, % by
weight, based on starting material II.
Examples of suitable bases are potassium hydrox-
ide, sodium hydroxide, potassium carbonate, sodium
carbonate, lithium hydroxide, lithium carbonate, sodium
bicarbonate, potassium bicarbonate, calcium hydroxide,
calcium oxide, barium oxide, magnesium hydroxide, mag-
nesium oxide, barium hydroxide, calcium carbonate,
magnesium carbonate, magnesium bicarbonate, magnesium
acetate, zinc hydroxide, zinc oxide, zinc carbonate, zinc
bicarbonate, zinc acetate, sodium fonnate, sodium
acetate, trimethylamine, triethylamine, tripropylamine,
triisopropylamine, tributylamine, triisobutylamine, tri-
sec-butylamine, tri-tert-butylamine, tribenzylamine,
tricyclohexylamine, triamylamine, trihexylamine, N,N-
dimethylaniline, N,N-diethylaniline, N,N-dipropylaniline,
N, N-dimethyltoluidine, N, N-diethyltoluidine, N, N-
2 0 dipropyltoluidine, N, N-dimethyl-4-aminopyridine, N, N-
diethyl-4-aminopyridine, N,N-dipropyl-4-aminopyridine,
N-methylpyrro l idine, N-ethylpyrrol idine, N-methyl -
piperidine,N-ethylpiperidine, N-methylimidazole, N-
ethylimidazole, N-methylmorpholine, N-ethylmorpholine,
2 5 N-methylhexamethyleneimine, N-ethylhexamethyleneimine,
pyridine, quinoline, alpha-pico1ine, beta-picoline,
isoquinoline, pyrimidine, acridine, N,N,N' ,N'-
tetramethylethylenediamini~, N, N, N ', N ~ -
tetraethylethylenediamine, quinoxaline,N-
3 0 propyldiisopropylamine / N, N-dimethylcyc lohexylamine, 2, 6 -
lutidine, 2,4-lutidine, trifurfurylamine or
triethylenediamine .
PrOCe5S BD
The compounds of the formula I are also obtained,
for example, by first reacting an oxalylhydroxylamine of
the general formula IV with an alkylating agent of the
formula V in a conventional manner in an inert organic

~ Q ~ 9
- 6 - o.Z. 0050/41753
solvent and, where R2 is not hydrogen, reacting the
resulting oxalylhydroxamic acid derivative Ia with an
alkylating agent of the general formula VI in a conven-
tional manner in an inert organic solvent.
Rl-Y R2_Y
HON(H)-CO-CO-X R3 ---- Rl-oN(H)-co-co-)~-R3 -- Rl-ON(R2)-Co-co-x-R3
IV V Id Vl
In the formulae V and VI, Y is a nucleophilically
displaceable leaving group, such as halogen, eg.
chlorine, bromine or iodine, or alkyl- or arylsulfonyl,
such as p-toluenesulfonyl.
The reaction is carried out in general at from
-10 to 100C, preferably from 0 to aooc.
Examples of suitable solvents are those stated
above for Proces~ A. The following are particularly
suitable: toluene, acetone, methyl ethyl ketone, diox-
ane, tetrahydrofuran, diethyl ether, methylene chloride,
1,1,l-trichloroethane and dLmethylformamide.
Suitable bases in this process, in addition to
those stated above, are lithium hydride and sodium
hydride.
In view of the intended use of the compounds IA,
suitable substituents are the following radicals:
X is oxygen or sulfur, preferably oxygen;
R1 is Cl-C20-alkyl, preferably branched or straight-chain
Cl-C4-al~yl, such as methyl, ethyl, propyl, l-methylethyl,
butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dLmethylethyl,
pentyl, l-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-
dimethylpropyl, i-ethylpropyl~ hexyl, 1,l-dimethylpropyl,
1,2-dimethylpropyl, l-methylpentyl, 2-methylpentyl, 3-
methylpentyl, 4-methylpentyl, 1~1-dLmethylbutyl, 1,2-
dimethylbutyl, 1,3-dimethylbutyl, 2,2-dLmethylhutyl, 2,3-
dimethylbutyl, 3,3-dLmethylbutyl, l-ethylbutyl, 2-ethyl-
butyl, 1,1,2-trLmethylpropyl, 1,2,2-trLmethylpropyl, 1-
ethyl-1-methylpropyl or l-ethyl-2-methylpropyl, prefer-
ably branched or straight-chain C1-C4~alkyl, such as

~G~9
- 7 - O.Z. 0050/41753
methyl, ethyl, propyl, l-methylethyl, butyl, l-methyl-
propyl, 2-methylpropyl or 1,1-dimethylethyl,
C3-Cl8-alkenyl, in particular C3-C6-alkenyl, such as 2-
propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-
methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-
methyl-2-butenyl,2-methyl-2-butenyl,3-methyl-2-butenyl,
1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-
butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propen-
yl, l-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl,
5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-
methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-
pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-
methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-
pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-
dimethyl-2-butenyl,l,l-dimethyl-3-butenyl,1,2-dimethyl-
2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-
butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl,
2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-
dimethyl-2-butenyl,l-ethyl-2-butenyl,l-ethyl-3-butenyl,
2-ethyl-2-butenylj 2-ethyl-3-butenyl, l,1,2-trImethyl-2-
propenyl, l-ethyl-l-methyl-2-propenyl or l-ethyl-2-
methyl-2-propenyl, preferably 2-propenyl, 2-butenyl or 2-
methyl-2-propenyl, in particular 2-propenyl or 2-methyl-
2-propenyl,
or
C3-Ca-alkynyl, preferably C3-C6-alkynyl, such as 2-
propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-
pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-
methyl-3-butynyl, 2-methyl-3-butytnyl, 1,1-dimethyl-2-
propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-
hexynyl, 5-hexynyl~ l-methyl-2-pentynyl, 1-methyl-3-
pentynyl, l-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-
methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-
pentynyl,1,1-dimethyl-2-butynyl,l,1-dimethyl-3-butynyl,
1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-
2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl or 1-
ethyl-l-methyl-2-propynyl, preferably 2-propynyl or 2-

2 ~ Q~
- 8 - O.Z. 0050/41753
but-ynyl,
where these groups may carry from one to five halogen
atoms, such as fluorine, chlorine, bromine or iodine,
preferably fluorine, chlorine or bromine, in particular
chlorine or bromine,
C2-C~-alkyl, in particular C2-C6-alkyl as stated above,
which carries a Cl-C12-alkoxy group, preferably a Cl-C8-
alkoxy group, in particular a C1-C6-alkoxy group, such as
methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-
methylpropoxy, 2-methylpropoxy, l,l-dimethylethoxy,
pentyloxy, l-methylbutoxy, 2-methylbutoxy, 3-methyl-
butoxy, 1,l-dLmethylpropoxy, 1,2-dimethylpropoxy, 2,2-
dimethylpropoxy, l-ethylpropoxy, hexyloxy, l-methylpent-
yloxy, 2-methylpentyloxy, 3 methylpentyloxy, 4-methyl-
pentyloxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-
dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxyj
3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-
trimethylpropoxy, 1,2,2-trimethylpropoxy, l-ethyl-l-
methylpropoxy or 1-methyl-2-methylpropoxy,
monocyclic or polycyclic C3-C10-cycloalkyl, such as
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo-
heptyl, cyclooctyl, menthyl, norbornyl, adamantyl or
tricyclodecanyl, preferably cyclopropyl, cyclopentyl or
cyclohexyl, in particular cyclohexyl,
or monocyclic or polycyclic C3-C10-cycloalkylmethyl, such
as cyclopropylmethyl, cyclobutylmethyl, cyclopentyl-
methyl, cyclohexylmethyl, cycloheptylmethyl or cyclooct
ylmethyl, preierably cyclopropylmethyl, cyclopentylmethyl
or cyclohexylmethyl, in particular cyclohexylmethyl,
where these rings may carry from one to three C1-C4-alkyl
groups, such as methyl, ethyl, propyl, l-me~hylethyl,
butyl, l-methylpropyl, 2-methylpropyl or 1,1-dimethyl-
ethyl, preferably methyl, ethyl or l-methylethyl, in
particular meth~l,
and/or one phenyl ringf
phenyl or phenyl-Cl-C4-alkyl, such as benzyl, 1-phenyl-
ethyl, 2-phenylethyl, l-phenylpropyl, 2-phenylpropyl, 3-

7 J 9
- g - o.z. 0050/41753
phe~ylpropyl, l-methyl-~-phenylethyl, 1-methyl-1-phenyl-
ethyl, l-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-
phenylbutyl, l-methyl-l-phenylpropyl, l-methyl-2-phenyl-
propyl,l-methyl-3-phenylpropyl,2-methyl-1-phenylpropyl,
S 2-methyl-2-phenylpropyl, 2-methyl-3-phenylpropyl or 1,1-
dimethyl-2-phenylethyl,
where the aromatic radicals may carry from one to five
halogen atoms, such as fluorine, chlorine, bromine or
iodine, preferably fluorine, chlorine or bromine, and/or
from one to three of the following groups: nitro,
C1-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl,
butyl, l-methylpropyl, 2-methylpropyl or l,l-dimethyl-
ethyl, preferably methyl, ethyl, l-methylethyl or 1,1-
dimethylethyl, in particular methyl or ethyl,
Cl-C4-haloalkyl, in particular Cl- or C2-haloalkyl, such as
chloromethyl, dichloromethyl, trichloromethyl, fluoro-
methyl, difluoromethyl, trifluoromethyl, chlorofluoro-
methyl, dichlorofluoromethyl, chlorodifluoromethyl, l-
fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-
trifluoroethyl, 2-chloro-2-fluoroe~hyl, 2-chloro-2,2-
difluoroethyl, 2,2-dichioro-2-fluoroethyl, 2,2,2-tri-
chloroethyl or pentafluoroethyl, preferably trifluoro-
methyl,
Cl-C4-alkoxy, such as me~hoxy, ethoxy, propoxy, l-methyl-
ethoxy, butoxy, l-methylpropoxy, 2-methylpropoxy or 1,l-
dimethylethoxy, preferably methoxy or ethoxy,
C1-C4-haloalkoxy, in particular Cl- or C2-haloalkoxy, such
as chloromethoxy, dichloromethoxy, trichloromethoxy,
fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro-
fluoromethoxy,dichlorofluoromethoxy,chlorodifluorometh-
oxy, l-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy,
2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy,2-chloro-
2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-
trichloroe~hoxy or pentafluoroethoxy, preferably di-
fluoromethoxy or trifluoromethoxy,
C1-C4-alkylthio, such as methylthio, ethylthio, propyl-
thio, 1-methylethylthio, butylthio, l-methylpropylthio,

~A~ ~j9
- 10 - O.Z. 0050/41753
2-methylpropylthio or l,l-dimethylethylthio, preferably
methylthio, ethylthio, propylthio, butylthio or 2-methyl-
propylthio,
or Cl-C4-haloalkylthio, in particular Cl~ or C2-haloalkyl-
thio, such as chloromethylthio, dichloromethylthio,
trichloromethyl~ho,fluoromethylthio,difluoromethylthio,
trifluoromethylthio, chlorofluoromethylthio, dichloro-
fluoromethylthio, chlorodifluoromethylthio, 1-fluoro-
ethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio,
2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio,
2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-
fluoroethylthio, 2,2,2-trichloroethylthio or
pentafluoroethylthio;
R2 is hydrogen,
C1-C4-alkyl, such as methyl, ethyl, propyl, 1-methylethyl,
butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethyl-
ethyl, preferably me~hyl or ethyl;
C3- or C4-alkenyl, su~h as 2-propenyl, 2-butenyl, 3-
butenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl or
benzyl, where the aromatic radical may carry from one to
five halogen atoms, such as fluorine, chlorine, bromine
or iodine, preferably fluorine, chlorine or bromi~e,
and/or from one to three of the following groups:
C1-C4-alkyl, such as methyl, ethyl, propyl, l-methylethyl,
butyl, 1-methylpropyl, 2-methylpropyl or l,l-dimethyl-
ethyl, preferably methyl, ethyl, l-methylethyl or 1,1-
dimethylethyl, in particular methyl or ethyl,
Cl-C4-haloalkyl, in particular Cl- or C2-haloalkyl, such a~
chloromethyl, dichloromethyl, trichloxomethyl, fluoro-
methyl, difluoromethyl, trifluoromethyl, chlorofluoro-
methyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-
fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-
trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-
difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-tri-
chloroethyl or pentafluoroethyl,
Cl-C4-alkoxy, such as methoxy, ethoxy, propoxy, l-methyl-
ethoxy, butyoxy, l-methylpropoxy, 2-methylpropoxy or 1,1-

s~ 9
- 11 - o.z. 0050/41753
dimethylethoxy,
C1-C4-haloalkoxy, in particular Cl- or C2-haloalkoxy, such
as chloromethoxy, dichloromethoxy, trichloromethoxy,
fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro-
fluoromethoxy, dichlorofluoromethoxy,
chlorodifluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy,
2, 2-dif luoroethoxy, 2, 2, 2-trifluoroethoxy, 2-chloro-2-
f luoroethoxy, 2-chloro-2, 2-dif luoroethoxy, 2, 2-dichloro-
2 - f luoroethoxy, 2, 2, 2 -trichloroethoxy or
pentaf luoroethoxy,
C1-C4-alkylthio, such as methylthio, ethylthio, propyl-
thio, l-methylethylthio, butylthio, 1-methylpropylthio,
2-methylpropylthio or 1, l-dimethylethylthio,
or C1-C4-haloalkylthio, in particular Cl- or C2-haloalkyl-
thio, such as chloromethylthio, dichloromethylthio,
trichloromethylthio, f luoromethylthio,
d i f l u o r o m e t h y l t h i o , t r i f l u o r o m e t h y l t h i o ,
chlorof luoromethylthio, dichlorof luoromethylthio,
chlorodifluoromethylthio, 1-fluoroethylthio, 2-
f luoroethylthio, 2, 2-dif luoroethylthio, 2, 2, 2 -
trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-
2, 2-difluoroethylthio, 2, 2-dichloro 2-fluoroethylthio,
2, 2, 2 -trichloroethylthio or pentaf luoroethylthio,
and R3 is C1-C20-alkyl, preferably branched or straight-
2 5 chain Cl-Cl6-alkyl, such a~ methyl, ethyl, propyl, 1-
methylethyl, butyl, l-methylpropyl, 2-methylpropyl, 1,1-
dimethylethyl, pentyl, l-me~hylbutyl, 2-methylb~tyl, 3-
methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl,
1, l-dimethylpropyl, 1, 2-dimethylpropyl, l-methylpentyl,
2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-
dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylhutyl, 2, 2-
dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-
ethylbutyl, 2-e~hylbutyl, 1,1, 2-trimethylpropyl, 1, 2, 2-
trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-
methylpropyl, preferably straight-chain or branched
C1-C4-alkyl, such as methyl, ethyl, propyl, 1-methylethyl,
butyl, l-methylpropyl, 2-methylpropyl or 1, l-dimethyl-

~6 ~
- 12 - o.Z. 0050/41753
ethyl, octyl, 2-ethylhexyl, nonyl, decyl, dodecyl,
tetradecyl or hexadecyl,
which may carry from one to five halogen atoms, such as
fluorine, chlorine, bromine or iodine, preferably fluor-
ine, chlorine or bromine, in particular fluorine orchlorine, and/or from one to three of the following
groups:
cyano,
Cl-C10-alkoxy, such as methoxy, ethoxy, propoxy, 1-methyl-
ethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-
dimethylethoxy, pentyloxy, 1-methylbutoxy, 2-methyl-
butoxy, 3-methylbutoxy, l,1-dimethylpropoxy, 1,2-di-
methylpropoxy, 2,2-dimethylpropoxy, l-ethylpropoxy,
hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 3-methyl-
pentyloxy, 4-methylpentyloxy, 1,1-dLmethylbutoxy, 1,2-
dimethylbutox~, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy
2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy,
2-ethylbutoxy, 1,1,2-trLmethylpropoxy, 1,2,2-trimethyl-
propoxy, 1-ethyl-1-methylpropoxy, 1-ethyl-2-methyl-
propoxy, heptyloxy, octyloxy, 2~ethylhexyloxy, nonyloxy
or decyloxy,
ClC4-haloalkoxy, in particular Cl- or C2-haloalkoxy, such
as chloromethoxy, dichloromethoxy, trichloromethoxy,
fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro-
fluoromethoxy,dichlorofluoromethoxy,chlorodifluorometh-
oxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy,
2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy,2-chloro-
2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-
trichloroethoxy or pentafluoroethoxy,
Cl-C4-alkylthio, such as methylthio, ethylthio, propyl-
thio, l-methylethylthio, butylthio, l-methylpropylthio,
2-methylpropylthio or 1,1-dimethylethylthio, preferably
methylthio or ethylthio,
Cl-C4-haloalkylthio, in particular Cl- or C2-haloalkylthio,
such as chloromethylthio, dichloromethylthio, trichloro-
methylthio, fluoromethylthio, difluoromethylthio,
trifluoromethylthio, chlorofluoromethylthio, dichloro-

~4~7~9
- 13 - o.z. OOSO/41753
fluoromethylthio, chlorodifluoromethylthio, l-fluoro-
ethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio,
2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio,
2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-
fluoroethylthio, 2,2,2-trichloroethylthio or
pentafluoroethylthio, preferably trifluoromethylthio,
C3-ClO-cycloalkyl, such as cyclopropyl, cyclobutyl,
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, menth-
yl, norbornyl, adamantyl or tricylcodecanyl, preferably
cyclopropyl, cyclopentyl or cyclohexyl,
C3-C10-cycloalkoxy, such as cyclopropoxy, cyclobutoxy,
cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclo-
octyloxy, menthyloxy, norbornyloxy, adamantyloxy or
tricyclodecanyloxy, preferably cyclopropoxy, cyclopentyl-
oxy or cyclohexyloxy,
C3-C~O-cycloalkylthio, such as cyclopropylthio, cyclo-
butylthio, cyclopentylthio, cyclohexylthio, cycloheptyl-
thio, cyclooctylthio, menthylthio, norbornylthio,
adamantylthio or tricyclodecanylthio, preferably cyclo-
hexylthio,
or C3-Cl2-alkenyloxy, preferably C3-C3-alkenyloxy, in
particular C3-C6-alkenyloxy, such aR 2-propenyloxy, 2-
butenyloxy, 3-butenyloxy, 1-methyl-2-propenyloxy, 2-
methyl-2-propenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-
pentenyloxy, l-methyl-2-butenyloxy, 2-methyl-2-butenyl-
oxy, 3-methyl-2-butenyloxy, 1 methyl-3-butenyloxy, 2-
me~hyl-3-butenyloxy,3-methyl-3-butenyloxy,1,l-dimethyl-
2-propenyloxy, 1,2-dLmethyl-2-propenyloxy, 1-ethyl-2-
propenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-
hexenyloxy, l-methyl-2-pentenyloxy, 2-methyl-2-
pentenyloxy, 3-methyl-2-pentenyloxy, 4 methyl-2-
pentenyloxy, l-methyl-3-pentenyloxy, 2-methyl-3-
pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-
pentenyloxy,1-methyl-4-pentenyloxy,2-methyl-4-pentenyl-
oxy, 3-methyl-4-pentenyloxy, 4-methyl-4-pentenyloxy, 1,1-
dimethyl-2-butenyloxy, 1,2-dLmethyl-2-butenyloxy, 1,3-
dimethyl-2-butenyloxy, 2,3-dimethyl-2-butenyloxy, 1jl-

- 14 - o.Z. 0050/41753
dimethyl-3-butenyloxy, l.,2-dimethyl-3-butenyloxy, 1,3-
dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy, 2,3-
dLmethyl-3-butenyloxy, 1-ethyl-2-butenyloxy, 2-ethyl-2-
butenyloxy, 1-ethyl-3-butenyloxy, 2-ethyl-3-butenyloxy,
1,1,2-trimethyl-2-propenyloxy, 1-ethyl-1-methyl-2-
propenyloxy or l-ethyl-2-methyl-2-propenyloxy;
C3-C~8-alkenyl, in particular C3-C6-alkenyl, such as 2-
propenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-
propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-
2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-
methyl-3-butenyl,2-methyl-3-butenyl,3-methyl-3-butenyl,
l,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-
ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-
hexenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-
methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-
pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl J 4-
methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-
pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-
dimethyl-2-butenyl,1,1-dimethyl-3-butenyl,1,2-dLmethyl-
2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dLmethyl-2-
butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl,
2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-
dLmethyl-2-butenyl,l-ethyl-2-butenyl,l-ethyl-3-butenyl,
2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-
propenyl, 1-ethyl-l-methyl-2-propenyl or 1-ethyl-2-
methyl-2-propenyl, preferably 2-propenyl, 2-butenyl or 2-
methyl-2-propenyl
or C3-C8-alkynyl, in particular ~3-C6-alkynyl, such as 2-
propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-
pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-
methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-
propynyl, l-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-
hexynyl, 5-hexynyl, l-methyl-2-pentynyl, 1-methyl-3-
pentynyl, l-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-
methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-
pentynyl,l,l-dimethyl-2-butynyl,1,1-dLmethyl 3-butynyl,
1,2-dimethyl-3-butynyl, 2,2-dLmethyl-3-butynyl, 1-ethyl-

~Qa6759
- 15 - O.Z. 0050/41753
2-b~tynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl or 1-
ethyl-1-methyl-2-propynyl, preferably 2-propynyl,
where these groups may carry from one to five halogen
atoms, such as fluorine, chlorine, bromine or iodine,
preferably fluorine, chlorine or bromine;
monocyclic or polycyclic C3-C10-cycloalkyl, such as
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclo-
heptyl, cyclooctyl, menthyl, norbornyl, adamantyl or
tricyclodecanyl, preferably cyclopropyl, cyclopentyl or
cyclohexyl,
which may carry from one to three C1-C4-alkyl groups, such
as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-
propyl, ~-methylpropyl or l,l-dimethylethyl, preferably
methyl, ethyl or 1-methylpropyl;
phenyl-Cl-C4-alkyl, such as benzyl, 1-phenylethyl, 2-
phenylethyl, l-phenylpropyl, 2-phenylpropyl, 3-phenyl-
propyl, l-methyl-1-phenylethyl, l-methyl-l-phenylethyl,
l-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenyl-
butyl, 1-methyl-1-phen~lpropyl, 1-methyl-2-phenylpropyl,
1-methyl-3-phenylpropyl, 2-methyl-1-phenylpropyl, 2-
methyl-2-phenylpropyl, 2-methyl-3-phenylpropyl or 1,1-
dimethyl-2-phenylethyl, preferably benzyl, 2-phenylethyl
or 3-phenylpropyl,
or phenoxy-Cl-C4-alkyl, such as phenoxymethyl, l-pheno~y-
ethyl, 2-phenoxyethyl, 1-phenoxypropyl, 2-phenoxypropyl,
3-phenoxypropyl, l-methyl-1-phenoxyethyl, l-methyl-1-
phenoxyethyl, l-phenoxybutyl, 2-phenoxybutyl, 3-phenoxy-
butyl, 4-phenoxybutyl, l-methyl-l-phenoxypropyl, 1-
methyl-2-ph~noxypropyl, 1-methyl-3-phenoxypropyl, 2-
methyl-l-phenoxypropyl, 2-methyl-2-phenopxypropyl, 2-
methyl-3-phenoxypropyl or 1,1-dimethyl-2-phenoxyethyl,
preferably 2-phenoxyethyl,
where the aromatic radicals may carry from one to five
halogen atoms, such a~ fluorine, chlorin~ or iodine,
preferably fluorine, chlorine or bromine and/or from one
to three o~ the following groups: nitro,
Cl-C4-alkyl, such as methyl, ethyl, propyl, 1-methylethyl,

2~7~9
- 16 - O.Z. 0050/41753
butyl, l-methylpropyl, 2-methylpropyl or l,l-dimethyl-
ethyl, preferably methyl,
Cl-C4-haloalkyl, in particular Cl- or C2-haloalkyl, such as
chloromethyl, dichloromethyl, trichloromethyl, fluoro-
methyl, difluoromethyl, trifluoromethyl, chlorofluoro-
methyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-
fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-
trifluoroethyl, 2-chloro-2-fluoroethyl! 2-chloro-2,2-
difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-tri-
1~ chloroethyl or pentafluoroethyl, preferably tri-
fluoromethyl,
Cl-C4-alkoxy, such as methoxy, ethoxy, propoxy, l-methyl-
ethoxy, butoxy, 1 methylpropoxy, 2-methylpropoxy or 1,1-
dimethylethoxy, preferably methoxy or ethoxy,
Cl-C4-haloalkoxy, in particular Cl- or C2-haloalkoxy, such
as chloromethoxy, dichloromethoxy, trichloromethoxy,
fluoromethoxy, difluoromethoxy, trifluoromethoxy, chloro-
fluoromethoxy,dichlorofluoromethoxy,chlorodifluorometh-
oxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy,
2,2,2-trifluoroethoxy,2-chloro-2-fluoroethoxy,2-chloro-
2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-
trichloroethoxy or pentafluoroethoxy, preferably tri-
fluoromethoxy or ~ifluoromethoxy,
Cl-C4-alkylthio, ~uch a~ methylthio, ethylthio, propyl-
thio, 1-methylethylthio, butylthio, l-methylpropylthio,
2-methylpropylthio or 1,1-dLmethylethylthio, preferably
methylthio,
or
Cl-C4-haloalkylthio, in particular Cl- or C2-haloalkylthio,
3Q such ac chloromethylthio, dichloromethylthio, trichloro-
-methylthio, fluoromethylthio, difluoromethylthio, tri-
fluoromethylthio,chlorofluoromethylthio,dichlorofluoro-
methylthio, chlorodifluoromethylthio, l-fluoroethylthio,
2-fluoroe~hylthio/ 2,2-difluoroethylthio, 2,2,2-tri-
fluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-
2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio,
2,2,2-trichloroethylthio or pentafluoroethylthio,

17 O.Z. 0050/41753
preferably 2,2,2-trichloroethylthio.
Preferred compounds of the formula IA are those in which Rl has the
following meanings:
Cl-C20-alkyl as stated generally and specifically above;
C3-Clg-alkenyl, as stated generally and specifically above;
10 or C3-Cg-alkynyl, as stated generally and specifically above,
it being possible for these groups to bear from one to five halogen atoms,
as state~ generally and specifically above.
15 Further, compounds of the general formula IA are preferred in which R3
denotes one of the following radicals:
C1-C20-alkyl as stated generally and specifically above;
ZO C3-Clg-alkenyl, as stated generally and specifically above;
or C3-Cg-alkynyl, as stated generally and specifically above,
it being possible for these groups to bear from one to five halogen atoms,
25 as stated generally and specifically above, or
monocyclic or polycyclic C3-Clo-cycloalkyl or C3-Clo-cycloalkylmethyl, as
stated generally and specifically above, which may bear from one to three
Cl-C4-alkyl groups, as stated generally and specifically above.
Further preferred compounds of the general formula IA are those in which
R2 is hydrogen or methyl, and compounds IA in which X is oxygen.
Particularly preferred compounds IA are those in which the substituents35 have the following meanings:
X is oxygen;
R1 is C3-C1g-alkenyl, as stated generally and specifically above, these
groups being able to bear from one to five halogen atoms, as stated
generally and specifically above;
R2 is hydrogen or methyl, and
R3 is Cl-C20-alkyl, as stated generally and specifically above,

~Q~ ~759
18 O.Z. 0050/41753
C3-CIg-alkenyl, as stated generally and specifically above,
or C3-Cg-alkynyl~ as stated generally and specifically above,
it being possible for these groups to bear from one to five halogen
atoms, as stated generally and specifically above,
or
monocyclic or polycyclic C3-C1o-cycloalkyl or C3-C1o-cycloalkylmethyl,
as stated generally and specifically above, which may bear from one to
three C1-C4-alkyl groups, as stated generally and specifically above.
Suitable salts of the compounds of the formula IA are agriculturally use-
15 ful salts, for example alkali metal salts, in particular the sodium or
potassium salt, alkaline earth metal salts, in particular the calcium,
magnesium or barium salt, the manganese, copper, ~inc or iron salt and
am~onium, phosphonium, sulfonium or sulfoxonium salts, for example
ammonium salts, benzyltrialkylammonium salts, trialkylsulfonium salts or
2~ trialkylsulfoxonium salts.
Examples of preferred oxalylhydroxamic acid derivatives of the general
formula IA are shown in the table below.

7 ~ 9
900236
19 O.Z. 0050/41753
Table
Compounds of the general formula IA
5 RI-oN(R2)-co-co-x-R3 IA
Rl R2 R3 X
CH3 CH3 C2Hs o
10 C2H5 C2H5 C2H5 0
C2H5 CH3 C2Hs o
C2H5 C2H5 C2H5 5
C2H5 C2H5 n~C3H7
C2H5 C2H5 CH3 o
15 n-C3H7 n~C3H7 C2Hs o
n~C3H7 n~C3H7 C2H5 S
CH~ CH3 n~C3H7
CH3 CH3 n-C4Hg
C2H5 C2H5 n~C4H9
20 C2H5 C2H5 i-C4H9
c~3 CH3 n-C6H13
Allyl Allyl . n-C6H13
CH3 CH3 H(CH2)4CH(c2H5)cH2
C2H5 C2H5 n-C8H17
25 CH3 CH3 n-C8H17
n~C3H7 n~C3H7 n-C8H17
Allyl Allyl n-C8H17
CH3 CH3 n-C9H19
CH3 CH3 n-CloH2l
30 C2H5 C2H5 n-C12H25
C2H5 c2~5 n-C12H25 S
CH3 H CH3 O
C2H5 H CH3 o
n~C3H7 H CH3 o
35 i-C3H7 H CH3 O
CH2=CHCH2 H CH3 O
n-C4Hg H CH3 O
sec.-C4Hg H CH3 O
tert.-CC4Hg H CH3 O
40 CH2CH=CHCH3 H CH3 O
CH2CH=CHCH3 H CH3 S
CH2C(CH3)=cH2 H CH3 O
H2C=C(Cl)cH2 H CH3 O

h ~ 9
900236
O.Z. 0050/41753
Table (contd.)
R1 R2 R3 X
-
CICH=CHCH2 H CH3 o
5 H2C=C(Br)CH2 H CH3 O
(cH3)2c=cHcH2 H CH3 o
n-C6H13 H CH3 O
(CH3)3CCH2CH2 H CH3 O
n-C8H17 H CH3 O
10 CH3CH2CH2CH2CH(c2H5)cH2 H CH3 O
n-C14H29 H CH3 O
CyclopropyImethyl H CH3 O
Cyclopentyl H CH3 O
Cyclohexyl ~I CH3 O
15 4-Methylcyclohexyl H CH3 O
CyclohexyImethyl H CH3 O
4-tert.-Butylcyclohexyl H CH3 O
n~C3H7 H C2H5
n~C3H7 H C2H5 S
20 CH2=CHCH2 H C2H5
CH3CH=CHcH2 H C2H5
ClCH=CHCH2 H C2H5. O
CH2=C(C~cH2 H C2H5
CH2=C(Br)CH2 H C2H5
25 CH2=C(CH3)CH2 H C2H5
(cH3)2c=cHcH2 H C2H5
n-C4H9 H C2H5
i-C4Hg H C2H5
Cl-(CH2)3 H C2H5
30 Cl-(cH2)4 H C2H5
Br-(CH2)4 H C2H5
Cl-(CH2)6 H C2H5
n-CloH21 H C2H5
n-C16H23 H C2H5
35 CH3 H n-C3H7
C2H5 H n-C3H7 O
nc3H7 H n-C3H7 O
n~C3H7 H n-C3H7 O
i-C3H7 H n-C3H7
40 CH2=CHCH2 H n-C3H7
n-C4H9 H n-C3H7
i C4Hg H n-C3H7 O

5 ~
900236
21 O.Z. 0050/41753
Table (contd.)
Rl R2 R3 X
CH3CH=CHcH2 H n-C3H7 o
5 CH2=C(CH3)cH2 H n-C3H7 o
CH2=C(Cl)cH2 H n-C3H7 o
CH2=C(Br)CH2 H n-C3H7 o
(CH3)2c=cHcH2 H n-C3H7
n-C14H29 H n-C3H7 o
10 CH3 H CH2CH2CI o
C2H5 H CH2CH2Cl 0
n~C3H7 H CH2CH2C1 0
i-C3H7 H CH2CH2CI o
CH2=CHCH2 H CH2CH2CI 0
15 n-C4Hg H CH2CH2CI o
i-C4Hg H CH2CH2C1 0
CH3cH=cHcH2 H CH2CH2C1 0
CH2=C(CH3)cH2 H CH2CH2CI o
CH2=C~Cl~cH2 H CH2CH2Cl o
20 CH2=C(Br)CH2 H CH2CH2CI o
Cl-(CH2)3 H CH2CH2Cl 0
CH3 H n-C4Hg 0
CH3 H n-C4Hg S
C2H5 H n-c4H9
25 n-C3H7 H n-C4Hg 0
i-C3H7 H n-C4Hg 0
CH2=CHcH2 H n-C4H9
HC-CCH2 H n-C4Hg 0
n-C4Hg H n-C4Hg 0
3~ sec.-C4Hg H n-C4Hg 0
tert.-C4Hg H n-C4Hg 0
CH3CH=CHcH2 H n-C4Hg 0
CH2=CtCH3)cH2 H n-C4Hg 0
CH2=C(Cl)cH2 H n-C4Hg 0
35 CH2=C(Br)CH2 H n-C4H9
(CH3)2C=CHCH2 H n-C4Hg 0
Cycloppropyl H n-C4Hg 0
Cyclopropylmethyl H n-C4Hg 0
Cyclopentyl H n-C4Hg 0
40 Cyclohexyl H n-C4Hg 0
2-Cyclohexenyl ~ n-C4Hg 0
Cyclohexylmethyl H n-C4Hg O
4-Methylcyclohexyl H n-C4Hg 0

900236
22 O.~. 0050/41753
Table tcontd.)
Rl R2 R3 X
4-tert.-Butylcyclohexyl H n-C4Hg O
5 1-Decalyl H n-C4Hg O
2-Decalyl H n-C4Hg O
2-Norbornyl H n-C4Hg O
C6H5CH2 H n-c4H9
4-F-C6H4CH2 H n-C4Hg O
10 4-Cl-C6H4CH2 H n-C4Hg O
2-CI-C6H4CH2 H n-C4Hg O
3-CI-C6H4CH2 H n-C4Hg O
4-Br-C6H4CH2 H n-C4H9
2,4-C12-C6H3CH2 H n-C4Hg O
15 3,4-C12-C6H3CH2 H n C4H9
4-CH3-C6H4CH2 H n-C4Hg O
4-F3C-C6H4cH2 H n-C4Hg O
4-CH3O-C6H4CH2 H n-C4Hg O
4-O2N-C6H4CH2 H n-C4Hg O
20 4-tert.-c4H9-c6H4cH2 H n-C4~19
CH3 H i-C4Hg o
C2H5 H i-C4Hg O
n~C3H7 H i-C4Hg O
i-C3H7 H i-C4Hg O
25 CH2=CHCH2 H i-C4Hg O
HC-CCH2 H i-C4Hg O
H3CC=CHCH2 H i-C4Hg O
n-C4Hg H i-C4Hg O
i-C4Hg H i-C4Hg O
30 CH2=C(CH3)CH2 H i-C4Hg O
CH2=C(cl)~H2 H i-C4Hg O
CH2=C(Br)CH2 H i-C4Hg O
CltCH2)3 H i-C4Hg O
CH3OCH2CH2 H i-C4Hg O
35 CH3OCH2CH2cH2 H i-C4Hg O
C2H5OCH2cH2 H i-C4Hg O
n-C~H7OCH2cH2 H i-C4Hg O
C2H5 H CH2=CHCH2 O
n~C3H7 H CH2=CHcH2 O
40 i-C3H7 H CH2=CHCH2 O
CH2=CHCH2 H CH2=CHCH2 O
CH2=C(CH3)cH2 H CH2=CHCH2 O
C2H5 H CH3CH=CHCH2 O

5 9
900236
23 O.Z. 0050/41753
Table (contd.)
Rl R2 R3 X
n~C3H7 H CH3CH=CHCH2 O
5 CH2=CHCH2 H CH3CH=CHCH2 O
CH2=C(CH3)cH2 H CH3CH=CHCH2 O
C2H5 H CICH=CHCH2 O
n~C3H7 H CICH=CHCH2 O
CH2=CHCH~ H CICH=CHCH2 O
lO CH2=C(CH3)CH2 H CICH=CHCH2 O
C2H5 H (CH3)2C=CHCH2 o
n~C3H7 H (CH3)2C=CHCH2 O
CH2=CHCH2 H (CH3)2C=CHCH2 O
C2H5 H CgHl7CH=CHCH2
15 n-C3H7 H CgHl7CH=CHCH2 o
C2H5 H CloH2~CH=CHCH2
n~C3H7 H CloH2lcH=cHcH2
CH3 H n-C5Hll
C2H5 H n-CSHll
20 n-C3H7 H n-C5H11
i-C3H7 H n-C5Hll
n~C4H9 . H n-C5Hll O
CH2=CHCH2 H n-C5H11
CH2=C(CH3)CH2 H n-C5Hll
25 CH3 H n-C6Hl3
C2H5 H n-C6H13
n~C3H7 H n-C6H13
i-C3H7 H n-C6H13
CH2=CHcH2 H n-C6H13
30 HC_CCH2 H n-C5H13 o
CH2=C(CH3)CH2 H n-C6H13
C2H5 H CH3(CH2)3CH(C2H5)cH2
n~C3H7 H CH35CH2)3CH(c2H5)cH2
i-C3H7 H CH3(CH2)3CH(C2H5)cH2
35 CH2=CHCH2 H CH3(CH2)3CH(c2H5)cH2
CH2=C(CH3)cH2 H CH3(CH2)3CH(C2H5)cH2
n-C4Hg H CH3(CH2)3CH(c2H5)cH2
C2H5 H n-C8Hl7
C2H5 H n-C9H19
40 C2H5 H n-ClOH21
n~C3H7 H n-5loH2l
i-C3H7 H n-ClOH21
CH2=CHCH2 H n-ClOH21

~ ~ L~
900236
24 O.Z. 0050/41753
~able (contd.)
Rl -- ~ R2 R3 X
CH2=C(CH3)CH2 H n-ClOH21
5 C2H5 H n-C12H25
n~C3H7 H n-C12H25
i-C3H7 H n-C12H25
CH2=CHcH2 H n-C12H25
CH2=C(CH3)cH2 H n-C12H25
n-C4Hg H n-C12H25
C2H5 H n-C14H29
n~C3H7 H n-C14H29
i-C3H7 H n-C14H29
CH2=CHcH2 H n-C14H29
15 CH2=C(CH3)CH2 H n-C14H29
C2H5 H n-C16H33
n~C3H7 H n-C16H33
i-C3H7 H n-C16H33
CH2=CHcH2 H n-C16H33
20 CH2=C(CH3)CH2 H n-C16H33
n-C4Hg H n-C16H33
C2H5 H . n-C18H37
CH2=CHcH2 H n-C18H37
C2H5 H n-C20H41
25 C2H5 H n-C3H7O(CH2)3
C2H5 H n-c3H7o(cH2)4
C2H5 H n-C3H70(CH2)6
C2H5 H i-c3H7o(cH2)2
C2H5 H i-c3H7o(cH2)4
30 C2H5 H n-C4HgO(CH2)4 O
C2H5 H n-C4HgO(CH2)6
C2H5 H i-C4HgO(CH2)6
C2H5 H i-C4HgO(CH2)6
C2H5 H sec.-C4HgO(CH2)4
35 C2Hs H (cH3)3ccH2o(cH2)4
C2H5 H (CH3)3ccH2cH2o(cH2)4 O
C2H5 H n-c6Hl3o(cH2)4
C2H5 H (CH3)2CHCH2CH(c2H5)cH2O(cH2)4
C2H5 H n-c8Hl7o(cH2)4
40 C2H5 H n-CgHlgO(CH2)4
C2H5 H n-C10~21(CH2)4
C2H5 H cyclo-C5HgO(CH2)4

2 ~ 9
900236
O.Z. 0050/41753
~able (contd.)
R1 R2 R3 - X
C2H5 H cyclo-C6Hl1o(cH2)4
5 C2H5 H CH2=cHcH2o(cH2)4
C2H5 H CH2=C(cH3)cH20(cH2)4
C2H5 H (c~3)2c=cHcH2o(cH2)4
C2H5 H C6H5CH2
C2H5 H 4-F-C6H5CH2
10 C2Hs H 4Cl-C6H5CH2
C2H5 H 4BrC6H5CH2
C2H5 H 4CH3C6H5CH2
C2H5 H 4-CH30-C6H5CH2 0
C2H5 H 4-F3C-C6H4CH2 0
15 C2H5 H 4 Q2N-C6H4CH2
C2H5 H 4-tert.-C4Hg~C6H4~H2
C2H5 H 2 4-C12-C6H3CH2 0
C2H5 H Cyclopentyl 0
C2H5 H Cyclopentylmethyl 0
20 C2H5 H Cyclohexyl 0
C2H5 H Cyclohexylmethyl 0
C2H5 H 4-Methylcyclohexyl 0
C2H5 H 2-Methylcyclohexyl 0
C2H5 H 4-1sopropylcyclohexyl 0
2S C2H5 H 4-tert.-B~tylcyclohexyl 0
C2H5 H 2-Norbornyl 0
C2H5 H 1-Decalyl 0
C2H5 H 2-Cecalyl 0
CH3 H C2H5
30 C2H5 H C2H5
i-C3H7 H C2H5
C6H5CH2 H C2H5

2 ~ 5 9
26 o.Z. 0050/41753
The growth-regulating active ingredients IA, or agents containing them,
may be applied for instance in the form of directly sprayable solutions,
powders, suspensions (including high-percentage aqueous, oily or other
suspensions), dispersions, emulsions, oil dispersions, pastes, dusts,
5 broadcasting agents, or granules by spraying, atomizing, dusting, broad-
casting or watering. The forms of application depend entirely on the pur-
pose for which the agents are being used, but they must ensure as fine a
distribution of the active ingredients according to the invention as
possible.
For the preparation of solutions, emulsions, pastes and oil dispersions to
be sprayed direct, mineral oil fractions of medium to high boiling point,
such as kerosene or diesel oil, further coal-tar oils, and oils of vege-
table or animal origin, aliphatic, cyclic and aromatic hydrocarbons such
15 as toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphtha-
lenes and their derivatives, methanol, ethanol, propanol, butanol, cyclo-
hexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly
polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide,
N-methylpyrrolidone, water, etc. are suitable.
Aqueous formulations may be prepared from emulsion concentrates, pastes,
oil dispersions, wettable powders or water-dispersible granules by adding
water. To prepare emulsions, pastes and oil dispersions the ingredients as
such or dissolved in an oil or solvent may be homogenized in water by
25 means of wetting or dispersing agents, adherents or emulsifiers. Concen-
trates which are suitable for dilution with water may be prspared from
active ingredient, wetting agent, adherent, emulsifying or dispersing
agent and possibly solvent or oil.
30 Examples of surfactants are: alkali metal, alkaline earth metal and
ammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid,
phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalene-
sulfonic acid, and of fatty acids, alkyl and alkylaryl sulfonates, and
alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated
35 hexadecanols, heptadecanols, and octadecanols, salts of fatty alcohol
glycol ethers, condensation products of sulfonated naphthalene and
naphthalene derivatives with formaldehyde, condensation products of
naphthalene or naphthalenesulfonic acids with phenol and formaldehyde,
polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxyl-
40 ated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycolethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols,
isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated

~Q~759
27 O.Z. 0050/41753
castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene,
lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite
waste liquors and methyl cellulose.
5 Powders, dusts and broadcasting agents may be prepared by mixing or
grinding the active ingredients with a solid carrier.
Granules, erg., coated, impregnated or homogeneous granules, may be
prepared by bonding the active ingredients to solid carriers. Examples of
lO solid carriers are mineral earths such as silicic acids, silica gels,
silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole,
loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium
sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium
sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable
15 products such as grain meals, bark meal, wood meal, and nutshell meal,
cellulosic powders, etc.
The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % by
weight of active ingredient. The active ingredients are used in a purity
20 of from 90 to 100, preferably 95 to 100, % (according to the NMR
spectrum).
Examples of formulations are as follows:
25 I. 90 parts by weight of compound no. 32 is mixed with 10 parts by weight
of N-methyl-alpha-pyrrolidone. A mixture is obtained which is suitable for
application in the form of very fine drops.
II. 20 parts by weight of compound no. 17 is dissolved in a mixture
30 consisting of 80 parts by weight of xylene, 10 parts by weight of the
adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-
monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzene-
sulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene
oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts
35 by weight of water and uniformly distributing it therein, an aqueous dis-
persion is obtained containing 0.02% by weight of the active ingredient.
III. 20 parts by weight of compound no. 46 is dissolved in a mixture
consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of
40 isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide
and 1 mole of isooctylphenol, and 10 parts by weight of the adduct of
40 moles of ethylene oxide and 1 mole of castor oil. By pouring the
solution into 100,000 parts by weight of water and finely distributing it
therein, an aqueous dispersion is obtained containing 0.02% by weight of
the active ingredient.

2~759
28 O.Z. 0050/41753
IV. 20 parts by weight of compound no. 46 is dissolved in a mixture
consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a
mineral oil fraction having a boiling point between 210 and 280C, and
10 parts by weight of the adduct of 40 moles of ethylene oxide and I mole
5 of castor oil. By pouring the solution into 100,000 parts by weight of
water and uniformly distributing it therein, an aqueous dispersion is
obtained containing 0.02% by weight of the active ingredient.
V. 20 parts by weight of compound no. 17 is well mixed with 3 parts by
10 weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid,
17 parts by weight of the sodium salt of a lignin-sulfonic acid obtained
from a sulfite waste liquor, and 60 parts by weight of powdered silica
gel, and triturated in a hammer mill. By uniformly distributing the
mixture in 20,000 parts by weight of water, a spray liquor is obtained
15 containing 0.1% by weight of the active ingredient.
VI. 3 parts by weight of compound no. 32 is intimately mixed with
97 parts by weight of particulate kaolin. A dust is obtained containing 3%
by weight of the active ingredient.
VII. 30 parts by weight of compound no. 17 is intimately mixed with a
mixture consisting of 92 parts by weight of powdered silica gel and
8 parts by weight of paraffin oil which has been sprayed onto the surface
of this silica gel. A formulation of the active ingredient is obtained
25 having good adherence.
VIII. 20 parts by weight of compound no. 46 is intimately mixed with
2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a
fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenol-
30 sulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic
mineral oil. A stable oily dispersion is obtained.
IX. 95 parts by weight of compound no. 32 is mixed with 5 parts by weight
of N-methyl-a-pyrrolidone. A solution is obtained which is suitable for
35 application in the form of minute drops.
The growth-regulating active ingredients or the agents containing them may
be applied pre- or postemergence. If certain crop plants tolerate the
active ingredients less well, application techniques may be used in which
~0 the herbicidal agents are sprayed from suitable equipment in such a manner
that the leaves of sensitive crop plants are if possible not touched, and
the agents reach the soil or the unwanted plants growing beneath the crop
plants (post-directed, lay-by treatment).

2~6~5~
29 O.Z. 0050/41753
The application rates of active ingredient IA depend on the objective to
be achieved, the time of the year, the plants to be combated and their
growth stage, and are from 0.001 to 5.0, and preferably 0.1 to 3.0, kg of
active ingredient per hectare.
The active ingredients IA may influence virtually all development stages
of a plant, andf are therefore used as growth regulators. The diversity of
action of growth regulators depends especially on
10 a) the type and variety of plant;
b) the time applied, with reference to the development stage of the
plants and the time of the year;
c) the place and method of application (seed treatment, soil treatment,
or application to foliage~;
15 d) climatic factors, e.g., average temperature, amount of precipitation,
sunshine and duration;
e) soil conditions (including fertilization);
f) the formulation of the active ingredient; and
g) the concentration at which the active ingredient is applied.
A description of some of the various possibilities of using the growth
regulators according to the invention in agriculture and horticulture is
given below.
25 A. Vegetative plant growth can be inhibited to a considerable extent, a
fact which is manifested particularly in a reduction in plant height.
The treated plants thus have a compact habit; furthermore, the leaf
color is darker.
Of advantage in practice is for example the reduction in grass growth
on roadsides, hedges, canal embankments and on areas such as parks,
sportsgrounds, fruit orchards, lawns and airfields, thus reducing
expensive and time-consuming mowing.
A further feature of economic interest is the increase in the rigor of
crops which tend to lodge, such as cereals, Indian corn, sunflowers
and soybeans. The shortening and strengthening of the stem thus caused
reduces or eliminates the danger of lodging under unfavorable weather
conditions.
The use of growth regulators is also important for inhibiting plant
height and changing the time of ripening in cotton. It is thus pos-
sible for this important crop to be harvested completely mechanically.

7 ~ ~
O.Z. 0050/41753
In fruit and other trees, pruning costs can be reduced with growth
regulators. With growth regulators, it is also possible to break up
the alternate breeding rhythm of fruit trees.
Growth regulators may also increase or inhibit lateral branching. This
is of interest when, for instance in tobacco plants, it is desired to
inhibit the formation of lateral shoots (suckers) in favor of leaf
development.
With growth regulators, it is possible for instance in winter rape to
considerably increase the resistance to freeze injury. On the one
hand, upward growth and the development of a too luxuriant (and thus
particularly frost-susceptible) leaf or plant mass are inhibited; on
the other, the young rape plants are kept, in spite of favorable
growth conditions, in the vegetative development stage before winter
frosts begin. The danger of freeze injury is thus eliminated in plants
which tend to lose prematurely their inhibition to bloom and pass into
the generative phase. In other crops, too, e.g., ~inter cereals, it is
advantageous if the plants are well tillered in the fall as a result
of treatment with the compounds according to the invention, but enter
winter with not too lush a growth. This is a preventive measure
against increased susceptibility to freeze injury and - because of the
relatively low leaf or plant mass - attack by various (especially
fungus) diseases. The inhibition of vegetative growth also makes
closer planting possible in numerous crops, which means an increase in
yield, based on the area cropped.
B. Better yields both of plant parts and plant materials may be obtained with the novel agents. It is thus for instance possible to induce
increased formation of buds, blossom, leaves, fruit, seed grains,
roots and tubers, to increase the sugar content of sugarbeets,
sugarcane and citrus fruit, to raise the protein content of cereals
and soybeans, and to stimulate the increased formation of latex in
rubber trees.
The compounds of the formula I may raise the yield by influencing
plant metabolism or by promoting or inhibiting vegetative and/or
generative plant growth.
40 C. It is also possible with growth regulators to shorten or lengthen
growth stages and to accelerate or retard the ripening process in
plant parts either before or after harvesting.

7 ~j 9
31 O.Z. 0050/41753
A factor of economic interest is for example the facilitation of har-
vesting made possible by a chemical, temporally concentrated loosening
(abscission) of the adherence of stalks to the branches of citrus
fruit, olive trees, and other kinds of pomes, drupes and indehiscent
fruit. The same mechanism, i.e., promotion of the formation of separ-
ation layers between fruit or leaf and stem of the plant, is also es-
sential for a readily controllable defoliation of crop plants, e.g.,
cotton.
10 D. Further, transpiration in crop plants may be reduced with growth
regulators. This is particularly important for plants growing in
agricultural areas which are expensive to irrigate, e.g., in arid or
semi-arid areas. Irrigation frequency can be reduced by using the
compounds according to the invention, making for lower costs. AS a
result of the use of growth regulators, the water available can be
better utilized, because, inter alia,
- the size of the stomata opening is reduced;
- a thicker epidermis and cuticle are formed;
- penetration of the soil by the roots is improve~;
- the micro-climate in the stind is favorably influenced by the
more compact growth.
The active ingredients according to the invention may be applied not only
25 to the seed (as a dressing), but also to the soil, i.e., via the roots,
and - the method particularly preferred - to the foliage by spraying.
To increase the spectrum of action and to achieve synergistic effects, the
compounds of the formula IA according to the invention may be mixed with
30 each other, or mixed and applied together with numerous representatives of
other herbicidal or srowth-regulating active ingredient groups. Examples
of suitable components are diazines, 4H-3,1-benzoxazine derivatives, ben-
zothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiolcarbam-
ates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers,
35 triazinones, uracils, benzofuran derivatives, quinolinecarboxylic acids,
(hetero~-aryloxyphenoxypropionic acid derivatives (salts, esters, amides),
etc.
It may also be useful to apply the compounds of the formula IA, either a-
40 lone or in combination with other herbicides, in admixture with other crop
protection agents, e.g., agents for combating pests or phytopathogenic
fungi or bacteria. The compounds may also be mixed with solutions of
mineral salts used to remedy nutritional or trace element deficiencies.
Non-phytotoxic oils and oil concentrates may also be added.

2 ~ 9
32 O.Z. 0050/41753
Synthesis examples
The directions given in the examples below were employed, after appropri-
ate modifications to the starting materials, to obtain further active
5 ingredients IA. The compounds thus obtained are listed with their physical
details in the table below.
Example 1
10 Methyl r (methoxy)-methylamino]oxo-acetate
At 25C, 149.2 9 (1.53 mol) of O,N-dimethylhydoxylamine hydrochloride,
268.2 9 (3.28 mol) of sodium acetate and 133.2 9 (1.09 mol) of oxalic acid
monomethyl ester chloride were added one after the other to 1,500 ml of
15 acetic acid. After the mixture had been stirred for 12 hours at 25C, it
was suction filtered and the filtrate was evaporated down. 500 ml of ethyl
acetate was added to the residue, and the whole was then washed with 50 ml
of water, dried over Na25O4, evaporated down under reduced pressure and
fractionally distilled.
There was obtained 108.8 9 (68% of theory) of the title compound as a
colorless liquid; b.p. 82C/l mbar.
Example 2
Methyl (allyloxyamino)-oxo-acetate
13.3 g (0.11 mol) of allyl bromide was added to a suspension of 13.8 9
(0.1 mol) of potassium carbonate and 11.9 9 (0.1 mol) of methyl (hydroxy-
30 amino)-oxo-acetate in 110 ml of dimethylformamide, and the mixture was
stirred for 10 hours at 60C. The mixture was suction filtered, the
filtrate was evaporated down under reduced pressure, and the residue was
dissolved in 250 ml of ethyl acetate and washed with three times 25 ml of
water. Drying over Na2SO4 was followed by dissolution in ethyl acetate and
35 concentration under reduced pressure, finally at 80C and 0.2 mbar.
There was obtained 11.6 9 (73% of theory) of the title compound as a
colorless oil; nD2 1,4718.

2~7~9
.
o X
o ~
o _ C
, .
a~ ~ o _ co ~
E ~ ~ cr~ o ~ OD ~ ~ ~ ~_ o u
~D Vo~ ............................ c~l~ .~.
o ~ n. ~ '`IC~O~O~O~C:I~O~O~C~O~O'`JO~O~O~Or~JO ~ ~0 ~r) '`10
E n c:: ' ~ ~ c ~ ~ ~ ~ ~ ~ ~ s~ ~ c ~ _ ~ ~ ~
X oooooooooooooooooooo
V
,.,
C~
V
X
V
. I _.
I~ T
I I T I I T I O
O ~ VV VCLCV~-CCOVVVVVVVV
_.
I
I ~ I
~I ~~ T I T T I T T
V V C_~ V V V V V V C,> V T I I I I I I I I
I
V I
'I -- -- I
V
~ I V I
I I I -- V 11
t~ T T I ~ ~ ~ ~ ~7 ~ ~ V c~ ~ ~ ~ V
O v V V v O~ ~ V V v V v V C ! c +~ v I V
n . . ~ ~ ~ ~ r~ 03 ~ o ~ o ~ ~
sc o ._ ~ _ ~ _~ _ _ ~ _ _
~ ~ Z

~ O !~ 6 7 ~ ~
-
O X
O ~
O ~ _
o
O Q ~ c~ ~o~o~o~o~o~o~o~o~o-`lO~O~Or-O~O~O'`lO'`IOc`~o~o~oc`-Oo E ~ Cl: _ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
OOOOOOOOOOOOOOOOOOOOOO
T I T I T I I I I I I I T I I
~r) ~ I I O O O t~ ) ~ O ~ ) O O O O t-> V O V V t ~
~ I ~ I I I c ~ ~ L c ~ c ~ ~ ~ ~
tY I = I I I T I T I I T I I I I I I I T I I I
~`I I I I ~`I ~ I
I t_) O O I I V
-- ~ ~I I I ~-- --
L ~ I ~ ~t O I ~ L
~ m ~ ~ V I ~ 11 ~ C.~ al V
OC,) I I c ~ I I v I I V t_) V V O
~~,J ~ ~ T I ~`I T C~l I I ~ V ~ ~_) ~ V
n . .~ ~ u~ ~ o .~ o --
X O ~ ~ ~ ~ ~ ~ r~ ~ ~ ~ ~7
W Z

2 ~ 9
'o
-
cl:
u~ z
_I T
;t ~
O X
,n Iv
O ~
O ,_ ~
~ ._
E :~ ~ ~ o o
O _ ~ ~ ~ ~t ~ ~ o ~ ~ Ir) ~ ~ ~ ~ ;t ~ ~ ~ 1-- ;~ ~ ~ ~
o E ~ Cl~ ~o~o~lo ~ a~ In 03 ~o~C~ o~o~o ~ ~IQ~o~o~lo
OOOOOOOOOOOOOOOOOOOOOO
T
~n ~ ~ v c~
tr~ T I I I I -- -- --
I T T O ~ I I I ~ `J ~ T
V ~ ~ O O T I I I T I C ) c l V T I T I I ~r) ~ tt~
~: T T T I I T I I T T I I T I I I I I I I I I
I ~`J
I I t~l
~:i--C~
~ T ~ T I T T T I T ~ T
c- -- I -- T t~l ~I T ~1 1~1 I V t~l ~ I
_. _. I ~ ~ I I ~ ~ I I I I ~ T C~l C~ I
. . ~ ~ 1-- 0~ G O _ ~ ~ ~ u~ ~ r~ 00 :n o _~
~ ~ z

20A6 ia9
-
E
C ,_
_ ~
~: D
cr) ~:
U~ Z
,_ I .~
_ _ _ _
O X _ _
~1)
O _ ~ In ~D ~ ~
r~ ~ ~ O ~ m ~ ~ ~ ~D
E :~u-) ~ ID n ~ m ~
O ~ ._ID n In m ~ u~ _ _ _ _
_ ~ ~ ~ ~ ~ ~ ~ ~ ~ o ~ 1-- ~ ~ ~ V~ C~
~9 0 _ ~ ~ ~ C~
c~ ~ c I I I I I I I I I ~D ~ 00 m
o Q Q a.l ~ ~O~t~ o~o ~
o E n tl: c c c c ~ c ~ ~ ~ D
o
X ooooooooooooooooo o o
I I I I
~ n u~ n
I I I I
~ ~ ~.)
I T I I
'.D c~ m
________,_______~ ~ ~
T T X I I I I T T T T I Y Y Y Y
S.~C C C
I I I I I I I I I T I I I I I I I T
~`I I ~ I
I I l I
~J T ~J C~l _ C C_ -- T
-O T ~ I ~ I ~ I I I I I -- ~`J
O V 2 t`J I I I ~ ~ T ~ ~ _ ~ O O
I 11 ~ 1~ T 1~1 ~ 11 I
O ~1 T T ~ ~1 (`J V I I l~J ~ T C~l I ~ 111 1
_. _ _ T (_) ~1 I I I -- ~1 0 I . o T ~ I t
. . r. oo ~ o ~ ~ ~ ~ In ~ r~ o~ o o
~C O ~ ~ 0 0 0
Ll z

t~7~9
E
-
U~ Z
1-- I
~ _ _ _ __~_ _ _ _
O X V V E~ V V E V)
I
o v
O L~--
E ~ .~
o ~ ._ _ _ _ _ _ _ _ _
_ ~ ~ V~ V Vl ~ ~ ~ Vl V
~ o -- ~ _ _ _ _ ~_ _ _ _
_ L
o ~ o. c~ ~ ~a~ ~ o ~o ~ ~
o E ~ Cl: u~ ~D ~ ~ ~ ~ ~ ID
a~
X o o o o o o o o
C~
C ~ C
IY I X I I T
~ I ~ O
I t_~ T
I V ~ 1I T
~_) ~ I I I O
11 ~ I t~ t~
I I V
-- --~ 8~ U U
t~: t,~ V`~
. . ~0 O O
X O Ot~00 ~0COCr ~ ~ O~

fi 7 Aj 9
-
E
._
-
Z
I _ _ _ _ _ _ _
O x _ u~ ~ E //- _
O ~ D ~ ~D _ I
o _ ~a- o u~
~D
E ~.~
O ~ ._ ~
o-- u _ _ _ _ _ _ _
_ L a- U')C~ ~1 11'1 ~ _
g E ~ ~ ~ ~ ;~ ;i ~
o~
XO O O O O O O
o~
T I r
~ C~C~
r.J
LIC I I I T T
I
ll I
T T
~:1 . . ;1- U~
G X O ~) ~r. a ~, C1~ O- C~
LLI Z

2 ~ 9
E
~:L
c
._
-
Z
I
I _ _ _
o a) E E E
o ~ ~ ~ o
O _ r
._
~i D al ~I_ Ln
E :- .
O _ ~ ~
C~ o ~ _ _ _
o -- c
_ oo ,~
o c~
a~ E 1~ ~ t~ ;1' ~
X O O O
a~
r~
C~ V
~ C C
~: I T
S
O ~ ~ ~
X O O O O
_ 1~1 Z ~

O.Z. 0050/41753
Use examples
The growth-regulating action of the compounds of the general formula IA is
demonstrated in the following experiments.
The active ingredients were formulated
a) as a 0.1% strength solution in acetone, or
10 b) as a 10% strength emulsion in a mixture of 70wt% of cyclohexanol,
20wt% of Nekanil~ LN ~Lutensol~ AP6, a spreader-sticker with an
emulsifying and dispersing action based on ethoxylated alkylphenols)
and lOwt% of Emulphor~ EL (Emulan~ EL, an emulsifier based on
ethoxylated fatty alcohols)
and diluted to the desired concentration with acetone in the case of a)
and with water in the case of b).
The vessels employed were plastic flowerpots having a diameter of about20 12.5 cm and a volume of about 500 cm3 and were filled with a sandy loam
containing about 3.0~0 humus. The seeds of the test plants were sown
separately, according to species.
For the preemergence treatment, the formulated active ingredients were
25 applied to the surface of the soil immediately after the seeds had been
sown. The compounds were emulsified or suspended in water as vehicle, and
sprayed through finely distributing nozzles. After the agents had been
applied, the vessels were lightly sprinkler-irrigated to induce germin-
ation and growth. Transparent plastic covers were then placed on the
30 vessels until the plants had taken root. The cover ensured uniform germin-
ation of the plants.
For the postemergence treatment, the plants were grown, depending on
growth form, to a height of 3 to 15 cm before being treated with the com-
35 pounds, suspended or emulsified in water.
The pots were set up in the greenhouse, heat-loving species at 20 to 35C,
and species from moderate climates at 10 to 25C. The experiments were run
for from 2 to 4 weeks. During this period the plants were tended and their
40 reactionS to the various treatments assessed.
The growth-regulating action observed was confirmed at the end of the
experiment by measuring the growth height. The figures obtained were
compared with the growth height of untreated plants.

7 ~ 9
41 O.Z. 0050/41753
The comparative agent used for assessing the growth-regulating action was
N-(2-chloroethyl)-N,N,N-trimethylammonium chloride (Example A).
The plants used in the greenhouse experiments were: spring wheat ("Ralle"
5 variety), spring barley ("Aramir" variety), rice ("Bahia" variety), grass
("Apache" variety), sunflowers ~"Spanners Allzweck" variety), linseed and
cotton ("Stoneville 825" variety).
On postemergence application of 0.4 mg/vessel, compounds 2, 17, 18, 20,10 21, 23, 26, 30-33, 35, 38-40, 43 and 46 had a better action on spring
wheat, compounds 2, 17, 18, 20-23, 25, 26, 28, 30-35, 37-40, 43-49 and 51
a better action on spring barley, and compounds 20, 26, 38, 43 and 45 a
better action on rice, than prior art growth regulator A.
15 On postemergence application of 1.5 mg/vessel, compounds 20, 26 and 32 had
a better action on cotton and compound 16 a better action on linseed than
prior art growth regulator A.
On postemergence application of 6.0 mg/vessel, compounds 82 and 83 had a
20 better action on spring wheat and spring barley, compoun~ 20 had a better
action on grass, and compounds 2, 16-18, 20-23, 25, 26, 28, 30-33, 35,
37-39, 43, 45-49, 51, 58, 82 and 83 had a better action on sunflowers than
prior art growth regulator A.
25 The reduction in growth height was also accompanied by a deeper leaf col-
oration. The increased chlorophyll content is indicative of an increased
rate of photosynthesis, making for bigger yields.